Sodium borohydride → HCID 67346119, compound

HRID 1669483Notes

Reaction equation

HRID 1669483 reaction equation
[C:1]([O:5][C:6](=[O:38])[CH:7]=[CH:8][CH:9]1[CH2:16][N:15]2[C:17]3[CH:18]=[C:19]([C:30]([O:32][CH3:33])=[O:31])[CH:20]=[CH:21][C:22]=3[C:23]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[C:14]2[C:13]2[CH:34]=[CH:35][CH:36]=[CH:37][C:12]=2[O:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl.[Co](Cl)Cl>[C:1]([O:5][C:6](=[O:38])[CH2:7][CH2:8][CH:9]1[CH2:16][N:15]2[C:17]3[CH:18]=[C:19]([C:30]([O:32][CH3:33])=[O:31])[CH:20]=[CH:21][C:22]=3[C:23]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[C:14]2[C:13]2[CH:34]=[CH:35][CH:36]=[CH:37][C:12]=2[O:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 67344409HCID 67344409, compound

Product 1

HCID 67346119HCID 67346119, compound

Reagents, catalysts & solvents 3

HCID 24288Cobalt(II) chlorideCatalystHCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

Cobalt chloride hexahydrate (cat.; 0.12 eq) was added to a solution of methyl 7-[3-tert-butoxy-3-oxoprop-1-en-1-yl]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate in MeOH (0.02 M). Once the cobalt chloride was in solution, NaBH4 (5.4 eq) was introduced. Vigorous effervescence was noted, along with a darkening of the solution to grey/black. After circa 5 min, effervescence had subsided and the dark colour in the reaction began to dissipate with the reaction returning to yellow within 10 min. The reaction mixture was partitioned between EtOAc and 1N HCl (aq). The organics were washed with sat. aq. NaHCO3, water and brine before being dried (Na2SO4), filtered and concentrated in vacuo. The product was taken on without further purification (97%). (ES+) m/z 518 (M+H)+; 540 (M+Na)+.

Workup

  1. additionwas introduced
  2. waitAfter circa 5 min
  3. customyellow within 10 min
  4. customThe reaction mixture was partitioned between EtOAc and 1N HCl (aq)
  5. washThe organics were washed with sat. aq. NaHCO3, water and brine
  6. dry with materialbefore being dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product was taken on without further purification (97%)

Sources & evidence

ORD record
ord-fbcea537a5004810bf94931fdb7abe9e
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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